Co-condensate mixtures of iminoisoindolinones

ABSTRACT

Disclosed are pigments, being co-condensate mixtures of compounds of formula I, ##STR1## wherein R 1  is chlorine, bromine, fluorine, methyl, methoxy or ethoxy, preferably chlorine or methyl, 
     R 2  is hydrogen or has one of the significances of R 1 , preferably hydrogen, chlorine or methyl, 
     At least two of the compounds in said mixture being present in an amount of at least 0.1 mol per mol of mixture.

IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS

The invention provides pigments, being co-condensate mixtures ofcompounds of formula I, ##STR2## wherein R₁ is chlorine, bromine,fluorine, methyl, methoxy or ethoxy, preferably chlorine or methyl,

R₂ is hydrogen or has one of the significances of R₁, preferablyhydrogen, chlorine or methyl,

At least two of the compounds in said mixture being present in an amountof at least 0.1 mol per mol of mixture.

The preferred co-condensate mixtures consist of two compounds of formulaI, particularly such mixtures in which the mol % of one compound is from20 to 70 and of the other from 80 to 30.

Particularly preferred co-condensate mixtures are of compounds (a) and(b) of formula I, as follows:

Mixture 1--(a) R₁ and R₂ are chlorine; (b) R₁ is chlorine and R₂ ishydrogen.

Mixture 2--(a) R₁ and R₂ are chlorine (b) R₁ is chlorine and R₂ ismethyl.

Mixture 3--(a) R₁ and R₂ are chlorine (b) R₁ is methyl and R₂ ishydrogen.

Mixture 4--(a) R₁ is chlorine and R₂ is hydrogen (b) R₁ is chlorine andR₂ is methyl.

Mixture 5--(a) R₁ is chlorine and R₂ is hydrogen (b) R₁ is methyl and R₂is hydrogen.

Especially preferred is the mixture 1, above, in which the mol % ofcomponent (a) is 30% and the mol % of (b) is 70% of the co-condensatemixture.

The invention also provides a process for the production of theco-condensate mixture of the compounds of formula I, which processcomprises condensing a compound of formula II, ##STR3## wherein X = S,(o-alk)₂ or, preferably, NH, with at least two amines of formula III,##STR4## at least two of said amines being employed in an amount of atleast 0.1 mol per 2 mols of the compound of formula II.

The condensation may be carried out in conventional manner.

As will be appreciated, the mol % of individual component compounds inthe resulting co-condensate mixture is dependent on, and can be variedby adjusting, the mol % of the individual components in the mixture ofamines of formula III.

The co-condensates of the invention after, or even without, normalpigment conditioning are useful for pigmenting a wide variety ofmaterials, for example for in the mass pigmentation of syntheticplastics and resins such as of polyethylene, polystyrene,polyvinylchloride and synthetic leathers, with or without solvents, forthe pigmentation of rubber and spun viscose and cellulose acetate, forthe pigmentation of oil or water-based paints, for varnishes, lacquersand printing inks, for the pigmentation of paper in the stock and forthe coating and pigment printing of textiles.

The co-condensate mixtures provided by the invention almost invariablyhave a greater colour strength both than the individual components inthe mixtures and than simple admixtures of the components. This isbelieved to result from their better distribution in, for example,plastics and lacquer media.

The pigmentations produced employing the co-condensate mixtures of theinvention show good migration and light fastness as well as fastness toover-varnishing. They also have good transparency and heat resistanceproperties.

The following Examples, in which all parts and percentages are byweight, unless otherwise stated, and in which all temperatures are indegrees Centigrade, illustrate the invention.

EXAMPLE 1

A mixture consisting of 5,3 parts 2,513 -dichloro-1.4-diaminobenzene and10 parts 2-chloro-1,4-diamino-benzene (in a molar ratio of 30:70) issuspended in 300 parts trichlorobenzene and formed into a finesuspension by the introduction of 7,3 parts hydrogen chloride gas. 32Parts 3-iminoisoindolinone are then added. The whole is heated to 150°and stirred for 16 hours at this temperature. The yellow pigmentprecipitate which forms is filtered off at 100°, washed in successionwith hot trichlorobenzene, methanol and water and dried at 100°. Afterpulverising in a laboratory mill (or, for example, even in a coffeegrinder) the pigment mixture obtained is suitable for dyeing plasticsand varnishes. The dyeings have notable fastness to light, heat,migration and varnishing and, in addition, their depth of colour is25-30% higher than from a homogeneous pigment produced from 1 mol2,5-dichloro-1,4-diaminobenzene and 2 mols 3-imino-isoindolinone.

Compared with a homogeneous pigment produced from 1 mol 2-chloro-1,4-diaminobenzene and 2 mols 3-iminoisoindolinone, the dyeings obtainedwith the pigment mixture in Example 1 have an approximately 10% greaterdepth of colour and a significantly better resistance to heat. Moreover,there is no blooming when the mixture is used for dyeing plastics.

Application Example

0.5 Parts of the pigment mixture according to Example 1 and 5 partstitanium dioxide are added to a basic mixture consisting of

63 parts polyvinyl chloride (emulsion-type)

32 parts dioctyl phthalate,

3 parts commercial epoxy softener

1.5 parts stabiliser (barium-cadmium complex, likewise commercial grade)and

0.5 parts of a chelate former (commercial)

and the whole is intimately mixed.

To achieve better distribution of the pigment, the mixture is treatedfor 8 minutes on a roller frame heated to 160° and equipped withfriction rollers (one operating at 20 r.p.m. and the other at 25r.p.m.). The 0.3-mm. thick sheet obtained, which is yellow in colour, isthen removed. The dyeing has notable depth of colour, is notably fast tolight, migration and heat.

In the following Table A is given the relative colour strengths ofco-condendates produced in analogy with Example I but varying the mol %of the diamines employed. Also given are the relative colour strengthsobtained using the individual components of the co-condensate mixture(mol % of diamine I = 100 and mol % of diamine II = 100).

                  Table A                                                         ______________________________________                                        Diamine I                                                                              :     2,5-dichloro-1,4-diaminobenzene,                               Diamine II                                                                             :     2-chloro-1,4-diaminobenzene,                                   ______________________________________                                                   Relative colour strength in %                                      Mol ratio in %                                                                             Polyvinyl-                                                                              Alkydmela- Polyure-                                    No.  I     :     II    chloride                                                                              mine lacquer                                                                           thane                                 ______________________________________                                        1    100     --      100     100      100                                     2    70      30       96     102      106                                     3    60      40      107     103      105                                     4    50      50      117     114      121                                     5    40      60      116     121      128                                     6    30      70      124     123      129                                     7    20      80      117     114      116                                     8    --      100      90      96       94                                     ______________________________________                                    

In the following Tables B to D are given the results obtained in likemanner to as in Table A but employing different diamines and mixtures.

                  Table B                                                         ______________________________________                                        Diamine I                                                                              :     2,5-dichloro-1,4-diaminobenzene                                Diamine II                                                                             :     2-chloro-5-methyl-1,4-diaminobenzene                           ______________________________________                                                    Relative colour strength in %                                     Mol ratio in %                                                                              Polyvinyl-                                                                              Alkydmela- Polyure-                                   No.   I     :     II    chloride                                                                              mine lacquer                                                                           thane                                ______________________________________                                        1     100     --      100     100      100                                    2     90      10      103     114      123                                    3     80      20      104     109      124                                    4     70      30      136     130      135                                    5     60      40      160     144      144                                    6     50      50      135     138      152                                    7     40      60      139     149      159                                    8     30      70      168     155      173                                    9     20      80      168     152      159                                    10    --      100     120     118      121                                    ______________________________________                                    

                  Table C                                                         ______________________________________                                        Diamine  I                                                                             :     2,5-dichloro-1,4-diaminobenzene                                Diamine II                                                                             :     2-methyl-1,4-diaminobenzene                                    ______________________________________                                                    Relative colour strength in %                                     mol ratio in %                                                                              Polyvinyl-                                                                              Alkydmela- Polyure-                                   No.   I     :     II    chloride                                                                              mine lacquer                                                                           thane                                ______________________________________                                        1     100     --      100     100      100                                    2     90      10      105     105      103                                    3     80      20      106     110      112                                    4     70      30      122     140      148                                    5     60      40      131     141      154                                    6     50      50      121     131      139                                    7     40      60      110     119      116                                    8     30      70      129     131      127                                    9     20      80      141     141      141                                    10    --      100      76     105      103                                    ______________________________________                                    

                  Table D                                                         ______________________________________                                        Diamine  I                                                                             :     2-chloro-1,4-diaminobenzene                                    Diamine II                                                                             :     2-chloro-5-methyl-1,4-diaminobenzene                           ______________________________________                                                    Relative colour strength in %                                     mol ratio in %                                                                              Polyvinyl-                                                                              Alkydmela- Polyure-                                   No.   I     :     II    chloride                                                                              mine lacquer                                                                           thane                                ______________________________________                                        1     100     --      100     100      100                                    2     90      10      110     117      113                                    3     80      20      130     131      127                                    4     70      30      152     153      158                                    5     60      40      152     156      160                                    6     50      50      152     157      159                                    7     40      60      163     174      184                                    8     30      70      170     165      170                                    9     20      80      160     158      170                                    10    --      100     115     118      121                                    ______________________________________                                    

What is claimed is:
 1. A pigment, being a co-condensate mixture of two compounds of formula I, ##STR5## wherein R₁ is chloro, bromo, fluoro, methyl, methoxy or ethoxy, andR₂ is hydrogen or has one of the significances of R₁,wherein one of the compounds in said mixture is present in an amount of from 20 to 70 mol % and the other compound in an amount of from 80 to 30 mol %.
 2. A pigment according to claim 1, wherein, in the compounds of formula I, R₁ is chlorine or methyl.
 3. A pigment according to claim 1, wherein, in the compounds of formula I, R₂ is hydrogen, chlorine or methyl.
 4. A pigment according to claim 1, wherein said mixture consists of a first compound of formula I in which R₁ and R₂ are chlorine and a second compound of formula I in which R₁ is chlorine and R₂ is hydrogen.
 5. A pigment according to claim 1, wherein said mixture consists of a first compound of formula I in which R₁ and R₂ are chlorine and a second compound of formula I in which R₁ is chlorine and R₂ is methyl.
 6. A pigment according to claim 1, wherein said mixture consists of a first compound of formula I in which R₁ and R₂ are chlorine and a second compound of formula I in which R₁ is methyl and R₂ is hydrogen.
 7. A pigment according to claim 1, wherein said mixture consists of a first compound of formula I in which R₁ is chlorine and R₂ is hydrogen and a second compound of formula I, in which R₁ is chlorine and R₂ is methyl.
 8. A pigment according to claim 1, wherein said mixture consists of a first compound of formula I, in which R₁ is chlorine and R₂ is hydrogen and a second compound of formula I, in which R₁ is methyl and R₂ is hydrogen.
 9. A pigment according to claim 4, wherein said first compound is present in a mol% of 30 and said second compound in a mol% of 70 of the co-condensate mixture. 